Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses.
Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses.
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DOI：
10.1002/chem.201503510
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发表时间：
2015-11-02
期刊：
影响因子：
--
通讯作者：
Sheppard TD
中科院分区：
文献类型：
--
作者：
Foster RW;Tame CJ;Bučar DK;Hailes HC;Sheppard TD
l-阿拉伯糖是甜菜工业的一种丰富资源。通过使用基于腙的策略，l-阿拉伯糖被选择性脱水形成手性四氢呋喃在多克尺度上，而不需要保护基团。将此方法扩展到其他生物质来源的还原糖，并研究了关键环化的机制。该方法应用于一系列功能化手性四氢呋喃的合成，以及3r -3-羟基肌碱的正式合成。
l-Arabinose is an abundant resource available as a waste product of the sugar beet industry. Through use of a hydrazone-based strategy, l-arabinose was selectively dehydrated to form a chiral tetrahydrofuran on a multi-gram scale without the need for protecting groups. This approach was extended to other biomass-derived reducing sugars and the mechanism of the key cyclization investigated. This methodology was applied to the synthesis of a range of functionalized chiral tetrahydrofurans, as well as a formal synthesis of 3R-3-hydroxymuscarine.